Perilla seed composition

ABSTRACT

A composition of matter comprises a shelf stable, partially defatted supercritical CO 2  fluid solvent extracted whole grain flour derived from a cracked biomass of  perilla frutescens , the flour comprising minerals and 2 to 8 percent of native seed oil, 35 to 45 percent protein, and 35 to 45 percent fiber.

RELATED APPLICATION(S)

This is a continuation-in-part application of application Ser. No.13/231,131 filed Sep. 13, 2011, which is a continuation-in-partapplication of application Ser. No. 12/419,321 filed Apr. 7, 2009, whichis based upon provisional application Ser. No. 61/043,773 filed Apr. 10,2008, the disclosures which are hereby incorporated by reference intheir entirety.

FIELD OF THE INVENTION

This invention relates to plant-derived perilla seed products.

BACKGROUND OF THE INVENTION

The copending and commonly assigned U.S. patent application Ser. No.13/231,131 discloses a composition of matter that comprises a shelfstable, super critical, CO² fluid extracted seed oil derived from acracked biomass of perilla frutescens, the seed oil comprising fromabout 60 to about 95 percent w/w of PUFAs in a ratio of from about 4:1to about 6:1 alpha-linolenic acid (ALA) to linoleic acid (LA) and amixture of selected antioxidants.

A process for forming the perilla seed extract is also disclosed bysubjecting the pre-milled cracked or flake-rolled seed to supercriticalCO² extraction. A partially or wholly defatted perilla seed as a cakeresidue with virtually no fat or oil is disclosed as one of theby-products. The extracted oil in one example is the desired endproduct. The defatted cake resulting from the supercritical CO2 processis disclosed as potentially viable. It is desirable to process thepartially defatted cake to use as a dietary supplement, food orbeverage.

SUMMARY OF THE INVENTION

A composition of matter comprises a shelf stable, partially defattedsupercritical CO² fluid solvent extracted whole grain flour derived froma cracked biomass of perilla frutescens, the flour comprising mineralsand 2 to 8 percent of native seed oil, about 35 to 45 percent proteinand 35 to 45 percent fiber.

In one example, the native seed oil comprises 1 to 4 percent ALA andabout 0.2 to 0.8 percent LA. In another example, the fiber comprisesabout 32 to 40 percent insoluble fiber and about 2 to 6 percent solublefiber. The composition may exhibit pH dependent thixotropic propertieswhen mixed with water. The flour may further comprise lipophilicadditives comprising at least one of rosemary oil, tocopherols,tocotrienols, carotenoids, seed oils, lipophilic solvent extractedbotanical oils, lipophilic food flavorings, polyunsaturated fatty acidesters. In another example, the flour may further comprise hydrophilicadditives comprising at least one of hydrophilic solvent extracts ofbotanicals, green tea extract, grape seed extract, ascorbic acid,caffeine, mono and/or polysaccharides, gums, phospholipids, biopolymers,or hydrophilic food flavorings. The flour may comprise about 2 to 3percent of fructo-oligosaccharides in yet another example. A deliveryproduct may comprise a beverage, protein shake, nutritional bar,confectionary filling, icing, pasta, processed meat, peanut butter orjelly.

In another example, the composition of matter comprises a shelf stable,partially defatted, perilla frutescens derived, whole grain flourcomprising minerals and about 2 to B percent of native seed oil, about35 to 45 percent protein and about 35 to 45 percent fiber. The perillafrutescens derived, whole grain flour in one example is made bypre-milling or roller press flaking perilla frutescens seed in theabsence of oxygen to obtain a cracked seed biomass and subjecting thecracked seed biomass to supercritical fluid CO2 extraction to producethe flour with or without lipophilic and/or hydrophilic antioxidants.

A method is also disclosed of treating gastrointestinal irregularitiesand/or cardiovascular disease in humans or animals by administering aneffective amount of a dietary supplement, food or beverage that hasadded thereto the composition mixed therewith and comprising a shelfstable, partially defatted supercritical CO2 fluid solvent extractedwhole grain flour derived from a cracked biomass of perilla frutescens,the flour comprising minerals and about 2 to 8 percent of native seedoil, about 35 to 45 percent protein and about 35 to 45 percent fiber.

The method further comprises forming a beverage, liquid concentrate, ordried beverage pre-mix to which the composition is added. The methodfurther comprises preparing liquid concentrates or dried pre-mixesincluding protein shakes, fruit smoothies, ready-to-drink beverages, drybeverage pre-mixes, frozen fruit concentrates, aqueous alcoholicbeverage pre-mixes, concentrates or their dried pre-mixes, vitamin,carbohydrate and protein fortified meal replacement beverages, drinkabledairy and non-dairy yogurts, gravies and dry gravy pre-mixes, andready-to-drink and dried pre-mixed infant formulas. The method furthercomprises thickening the resulting final beverage by adding one or moreacidulants for adjusting the pH from between about 3 to about 6.5.

BRIEF DESCRIPTION OF THE DRAWINGS

Other objects, features and advantages of the present invention willbecome apparent from the detailed description of the invention whichfollows, when considered in light of the accompanying drawings in which:

FIG. 1 is a flowchart illustrating a production diagram as a flowchartfor producing omega-3 chia seed oil such as sold under the tradenameChia Gold™ by Valensa International of Eustis, Fla.

FIG. 2 is another production diagram as a flowchart showing basic stepsfor manufacturing a perilla seed extract in accordance with anon-limiting example.

FIG. 3 is another production diagram as a flowchart showing basic stepsfor manufacturing the perilla seed flour in accordance with anon-limiting example.

DETAILED DESCRIPTION OF THE EMBODIMENTS

The present invention will now be described more fully hereinafter. Thisinvention may, however, be embodied in many different forms and shouldnot be construed as limited to the embodiments set forth herein. Rather,these embodiments are provided so that this disclosure will be thoroughand complete, and will fully convey the scope of the invention to thoseskilled in the art.

It is well known in the literature that Polyunsaturated Fatty Acids(PUFAs) of all types are highly susceptible to peroxide, free radicaland light induced degradation including rancification and polymerizationmaking them unsuitable for human consumption. For example, it is wellknown that flax seed oil, also known as linseed oil, readily undergoesfree radical oxidation to advantageously form polymeric surfacesincluding oil based paints, hard furniture finishes and linoleumflooring. In addition, many companies offer flax seed oil for humanconsumption as a dietary supplement or food ingredient because of thehigh levels of PUFAs found in raw flax seed and its expeller pressedoils and more particularly Alpha-Linolenic Acid (ALA) and Linolenic Acid(LA). Many flax seed oil product labels suggest that the product must berefrigerated at all times due to the instability of such PUFAs in flaxseed oil. Careful examination of the majority of commercially availableflax seed oils obtained by expeller pressing, including those typicallystored under refrigerated conditions, unfortunately reveals that theyare unfit for human use based on their measured Peroxide Values (PVs).Such PV values above 3 meg/Kg (milliequivalents/gram) are deemed notsuitable for salad oil applications and PV values above 10 meq/Kg aredeemed to be unsuitable for human use because the measured PV value maybe an early indicator of rancidity and free radical induced degradation.On the other hand, PV values taken alone do not adequately characterizesuch oils since a low PV value can also be associated with PUFA's thathave already gone through the rancification process. Typical testing hasrevealed flax seed oil products sold for human consumption with observedPV's as high as 130 meq/kg also characterized with the odor associatedwith short chain aldehydes that make such oils “rancid” to olefactorysenses.

Most raw seed based oils in common cooking and baking use, such assoybean, corn and canola seed oils naturally contain enough PUFAs makingthem unsuitable, without further processing, for use as cooking oils.Therefore unless such PUFA containing raw seed oils are hydrogenated tofully saturated triglycerides using hydrogen and a catalyst prior totheir use in cooking applications, they are considered to be unfit foruse as cooking oils. These oils are typically first isolated by, forexample, expeller pressing the appropriate seed. The crude seed oil isthen filtered to remove biomass. The resulting oil, containingsignificant levels of PUFAs, is then catalytically hydrogenated toreduce the PUFA content to levels suitable for use of the resulting oilin cooking applications. If the hydrogenation process is incomplete,however, the resulting mixtures are found to contain both undesirableheat labile PUFAs that quickly undergo rancification to small chainaldehydes in the resulting heated cooking oil as well as unsaturatedtrans-fatty acids which are believed to be detrimental to animal andespecially human health.

Therefore, those skilled in the art will recognize the great difficultyin producing a shelf stable PUFA mixture wherein the PUFA content is ashigh as 70% wt/wt of the resulting seed extract from a natural seedsource that then exhibits extraordinary room temperature stability.

Commonly assigned and copending patent application Ser. No. 12/419,321discloses a Salvia hispanica L. derived seed oil extract composition ofmatter containing from 60-88% PUFAs in a ratio of from 3.1:1-3.3:1 ofALA to LA, 4-10% of C-18 mono-unsaturated fatty acid, 1-5% of C-18saturated fatty acid and 4-8% of C-16 saturated fatty acid in a mixedtriglyceride form stable at room temperature of 12-24 months containinga mixture of selected antioxidants. This chia derived composition has avery favorable ratio of ALA to LA (omega 3 to omega 6) of about 3.3:1 inone example.

Commonly assigned and copending U.S. patent application Ser. No.13/231,131 discloses a perilla seed oil extract that provides a healthysource of omega-3 and contains a very favourable ratio of ALA to LA(omega-3 to omega-6) of about 6:1 in one example. The perilla oil isobtained by pressing the perilla seeds to initiate seed cracking,processing the cracked biomass using supercritical CO² fluid extraction,and collecting the extract to deliver more of the higher molecularweight compounds.

This perilla seed derived flour is formed as a shelf stable,supercritical, CO² fluid extracted seed oil derived from a crackedbiomass of perilla frutescens, the seed oil comprising from about 60 toabout 95 percent w/w of PUFAs in a ratio of from about 4:1 to about 6:1alpha-linolenic acid (ALA) to linoleic acid (LA) and a mixture ofselected antioxidants.

In one example the selected antioxidants are formed as a synergisticmixture of selected lipophilic and hydrophilic antioxidants. In anotherexample the composition includes lipophilic antioxidants either alone orin combination with at least one of: a) phenolic antioxidants includingat least one of sage, oregano, and rosemary; b) tocopherol, c)tocotrienol(s), d) carotenoids including at least one of astaxanthin,lutein, and zeaxanthin; e) ascorbylacetate; f) ascorbylpalmitate g)Butylated hydroxytoluene (BHT); h) Docosapentaenoic Acid (BHA) and i)Tertiary Butyl hydroquinone (TBHQ). In another example a hydrophilicantioxidant or sequesterant is added comprising hydrophilic phenolicantioxidants including at least one of grape seed extract, tea extracts,ascorbic acid, citric acid, tartaric acid, and malic acid.

In an example the peroxide value of the seed oil is under 10.0 meg/Km.The composition may be supplemented with docosahexaenoic acid (DHA)and/or eicosapentaenoic acid (EPA) in pectin or gelatin basedconfectionary dietary supplement delivery systems. The composition mayinclude EPA, DHA, docosapentaenoic acid (DPA) or gamma-linolenic acid(GLA), fish oil, krill oil, krill oil concentrate, borage oil, eveningprimrose oil, olive oil or other plant, animal or algal based seed orfruit oils admixed therein. This seed oil may be shelf stable at roomtemperature up to 32 months.

A method is also disclosed of mitigating or preventing cardiovasculardisease, arthritic pain and inflammation, platelet aggregation, ortreating dry eye syndrome, premenstrual symptoms or modifying immuneresponse in humans or animals by applying an effective amount of adietary supplement, food or beverage that has added thereto acomposition mixed therewith and comprising a supercritical, CO² fluidextracted seed oil derived from a cracked biomass of perilla frutescens,the seed oil comprising from about 60 to about 95 percent w/w of PUFAsin a ratio of from about 4:1 to about 6:1 alpha-linolenic acid (ALA) tolinoleic acid (LA) and a mixture of selected antioxidants.

A method of manufacturing a perilla frutescens derived seed oil wasdisclosed with the seed oil comprising from about 60 to about 95 percentw/w of PUFAs in a ratio of from about 4:1 to about 6:1 alpha-linolenicacid (ALA) to linoleic acid (LA). The method included processing perillafrutescens seed preferably in the absence of oxygen to obtain a biomasshaving a desired particle size distribution, subjecting the resultingbiomass to supercritical fluid CO² extraction, collecting a resultingseed oil fraction, and separating water in the fraction.

The commonly assigned and copending patent application Ser. No.12/419,321 discloses the oil extract as a room temperature, shelf stablemixture of an approximate 3.1:1 to about 3.3:1 mixture ofalpha-linolenic acid (“ALA”, “Omega-3 polyunsaturated fatty acid”(“PUFA”)) to linoleic acid (“LA”, “Omega-6 PUFA) that has been preparedin the presence of limited amounts of saturated and mono-unsaturatedfatty acids as their mixed triglycerides by the use of eithersupercritical fluid CO² solvent extraction of pre-milled Salviahispanica L. seed alone, and more particularly, supercritical fluid CO²solvent extraction in the presence of mixtures of hydrophilic andlipophilic antioxidants, or, by the use of a common organic solventextraction such as hexane or by the use of expeller pressing techniques.The supercritical CO² extraction is preferred.

Such Omega-3 and Omega-6 PUFAs are well known as essential fatty acidsin man and many animals, which are useful in humans and animals inpromoting, for example, a heart healthy condition in man. It is alsowell known, however, that PUFAs are extremely susceptible to rapid,uncontrollable free radical mediated degradation.

The composition of matter disclosed in the copending '321 applicationincludes a supercritical CO² Salvia hispanica L. derived seed oilcomprising from 60-88% PUFAs in a ratio of from about 3.1:1-3.3:1 ofalpha-linolenic acid (ALA) to linoleic acid (LA), 4-10% of C-18mono-unsaturated fatty acid, 1-5% of C-18 saturated fatty acid and 4-8%of C-16 saturated fatty acid in a mixed triglyceride form that is stableat room temperature for 12-24 months and comprising a mixture ofselected antioxidants.

That composition of matter disclosed in the '321 application includesdietary supplement ingredients such as docosahexaenoic acid (DHA) and/oreicosapentaenoic acid (EPA) in pectin or gelatin based confectionarydietary supplement delivery systems. EPA, DHA, docosahexaenoic acid(DPA) or gamma-linolenic acid (GLA), fish oil, krill oil, krill oilconcentrate, borage oil, evening primrose oil, olive oil or other plant,animal or algal based seed or fruit oils are admixed therein eitheralone or in combination. Lipophilic antioxidants are added either aloneor in combination with at least one of a) phenolic antioxidantsincluding at least one of sage, oregano, and rosemary; b) tocopherol, c)tocotrienol(s), d) carotenoids including at least one of astaxanthin,lutein, and zeaxanthin; e) ascorbylacetate; f) ascorbylpalmitate g)Butylated hydroxytoluene (BHT); h) Docosapentaenoic Acid (BHA) and i)Tertiary Butyl hydroquinone (TBHQ). As disclosed, a hydrophilicantioxidant or sequesterant includes hydrophilic phenolic antioxidantsincluding at least one of grape seed extract, tea extracts, ascorbicacid, citric acid, tartaric acid, and malic acid.

A method of manufacturing and method of using the composition is alsoset forth in the '321 application.

As further disclosed in the incorporated by reference '321 application,this PUFA rich seed oil extract is prepared from Salvia hispanica L.seed which contains one of nature's more favorable seed basedconcentrations and ratios for the essential fatty acids, and morespecifically, the essential fatty acids ALA and LA in a ratio ofapproximately 3.3:1 as a mixture of ALA and LA that is stable at roomtemperature for long periods of time when desirably and appropriatelytreated with antioxidants either before, during, or after (or anycombination thereof). A shelf life of 12-24 months has been found.

Such oils are used either alone or advantageously in combination withother ingredients, for example, algae, plant or fish derivedalpha-linolenic acid (ALA) or linoleic acid (LA) metabolites such aseicosapentaenoic acid (EPA), docosapentaenoic acid (DPA),gamma-linolenic acid (GLA) or docosahexaenoic acid (DHA) or anycombination thereof, incorporated into appropriate foods, beverages ordietary supplements for the prevention or mitigation of such diseases ascardiovascular disease, arthritis, pain, blood clotting, dry eyes andbrain health.

Such disease mitigation has been associated with the competitive controlof the LA metabolic cascade and the resulting metabolic cascade productsfrom LA metabolism known commonly as eicosanoids, such as the series 2and 3 prostaglandins and thromboxanes, the series 4 leucotrienes andlipoxins and the series 5 leuotrienes all of which are potent plateletaggregators and/or inhibitors, pro-inflammatories, vasodilators,bronchoconstrictors, or anti-asthmatics and the like.

The consumption of ALA has been shown to be a very effective competitivesubstrate of delta-6 desaturase, which is known to be the rate limitingenzymatic step in both ALA and LA metabolism to the metabolic productsdiscussed above.

Attempted extraction of Saliva hispanica L. unmilled seed, usingsupercritical CO² even at extraordinarily high pressures of 1000 bar orhexane solvent at atmospheric pressures, yields very little, if any,seed oil, therefore the seed is milled prior to extraction. The extentof the milling, as measured by particle size distribution, isadvantageous to the extraction process in accordance with a non-limitingexample since the higher the surface area, the higher will be theefficiency and completeness of the extraction process by either organicsolvent based or supercritical fluid based processes. In addition, it isoften advantageous to mill the seed in a blanket of inert gas such asnitrogen to prevent per-oxidative processes from taking place that wouldotherwise be initiated in the presence of air or oxygen and light.

In one embodiment, whole seed is either first commutated in a standardknife or hammer mill or more preferably roller milled, preferably undera cold nitrogen atmosphere, to produce a cracked seed biomass. The seedbiomass is preferably treated with one or more hydrophilic and/orlipophilic antioxidants by mixing the antioxidants to the resultingbiomass. In another embodiment, the antioxidant may be advantageouslyadded to the seed prior to or during the milling process or at the pointof extraction without pre-blending the antioxidants evenly throughoutthe resulting biomass due to the nature of the extraction process. Thebiomass is then transferred to a supercritical fluid extraction unit forseparation of the seed oil from the cracked or flake-rolled biomass.

Alternatively, the pre-prepared biomass can be transferred to a commonhexane solvent extractor, or an expeller press for example, and the oilextracted from the biomass accordingly. Preferably either process isconducted in the absence of oxygen or air.

The supercritical fluid extraction of the milled seed admixed withhydrophilic and/or lipophilic antioxidants is accomplished by subjectingthe pre-milled cracked or flake-rolled seed to supercritical CO², or CO²and propane as a co-solvent, or supercritical propane alone at from40-1000 bar at from 30-100 Deg. C. More preferably the seed oil isextracted from the biomass between 50-800 bar at 50-90 deg. C. in suchCO² amounts measured in kgs/kg of biomass and for such times as may berequired to extract large portions of the seed oil content from thebiomass. In addition, entrainment solvents can be added to thesupercritical fluid to further enhance the efficacy of such extractions.For example, supercritical carbon dioxide extraction of the biomass canbe enhanced by the addition of propane to the supercritical extractionfluid.

The resulting seed oil dissolved in supercritical solvent(s) is nextallowed to fractionate in two separate pressure step-down stagesallowing the collection of a light and heavy fraction of seed oilextract. This light fraction also contains water that has beenco-extracted from the seed mass. The resulting seed oil, afterdegassing, is separated from any water that may have been carried overduring the extraction of the biomass containing the water. The lightfraction of the seed oil extract is rich in taste and odor componentsand may be admixed with the heavy fraction or may be discarded dependingon the desired product characteristics.

After separation of the water remaining in each fraction, the fractionsare then held under nitrogen or other inert gas and additional amountsof lipophilic and/or hydrophilic antioxidants may then be added. Inaddition, the resulting fractions may also be treated with bleachingclay, carbon and such other processing aids as may be required to renderthe oil suitable for its intended use in humans and animals.

The PV of the resulting seed oil extract is typically under 2.0 meq/Km,while accelerated decomposition, using a Rancimat instrument, remarkablyindicates an extrapolated room temperature shelf life of from about 1-2years. When the same process is repeated without the use ofantioxidants, the resulting PV is surprisingly under 10.0 meq/Kg mostprobably due to the use of supercritical CO² resulting in minimalexposure of the oil to oxygen species. However, the resulting oilquickly begins to build peroxide value in the presence of air even whenstored at temperatures of 0 begs. C. In addition, such unstabilizedoils, under accelerated rancimat testing exhibit very poor stability toheat and oxygen unlike the rancimat performance observed in stabilizedoils derived from the process described above.

The resulting supercritical fluid seed oil extract contains from 60-88%PUFAs in a ratio of from 3.1:1-3.3:1 of ALA:LA, 4-10% of C18mono-unsaturated fatty acid, 1-5% of C-18 saturated fatty acid and 4-8%C-16 saturated fatty acid composition in a mixed triglyceride formdepending on the seed source employed.

On the other hand, if the process described above is conducted withoutthe use of hydrophilic and/or lipophilic antioxidants, the resultingseed oil extract exhibits an initial low PV but accelerated stabilitytesting using a Rancimat instrument indicates an extrapolated roomtemperature shelf stability of less than two months.

The stability of the resulting oil at room temperature that ismanufactured without the use of added antioxidants is easily explainedbecause of the available levels of the powerful natural antioxidantsfound in Salvia hispanica L. whole seed whose activity can be easilymeasured in Oxygen Radical Absorbance Capacity (ORAC) units. Salviahispanica L. has a measured ORAC number of 3000 micromoles TE ORACunits/gram of seed and is known to contain such antioxidants asmyricetin, quercetin, kaempferol, caffeic acid, and chlorogenic acid. Inaddition, it is well known that the example Salvia hispanica L. wholeseed, unlike many other seeds bearing PUFA containing oil, exhibits ashelf life of at least 5 years due to its structure and the naturallyoccurring antioxidants available in the seed matrix.

In addition, cold pressing of Salvia hispanica L. whole seed alsoproduces unstable seed oil without careful addition of appropriateantioxidants to the seed prior to the expeller pressing process.

In a non-limiting example the composition of matter is formed from asupercritical CO² derived Salvia hispanica L. derived seed oilcomprising from 60-88% PUFAs in a ratio of from 3.1:1-3.3:1 ofalpha-linolenic acid (ALA) to linoleic acid (LA), 4-10% of C-18mono-unsaturated fatty acid, 1-5% of C-18 saturated fatty acid and 4-8%of C-16 saturated fatty acid in a mixed triglyceride form that is stableat room temperature for 12-24 months and comprising a mixture ofselected antioxidants.

It includes docosahexaenoic acid (DHA) and/or eicosapentaenoic acid(EPA) in pectin or gelatin based confectionary dietary supplementdelivery systems and in another aspect EPA, DHA, docosapentaenoic acid(DPA) or gamma-linolenic acid (GLA), fish oil, krill oil, krill oilconcentrate, borage oil, evening primrose oil, olive oil or other plant,animal or algal based seed or fruit oils are admixed therein.

Lipophilic antioxidants are added either alone or in combination with atleast one of a) phenolic antioxidants including at least one of sage,oregano, and rosemary; b) tocopherol, c) tocotrienol(s), d) carotenoidsincluding at least one of astaxanthin, lutein, and zeaxanthin; e)ascorbylacetate; f) ascorbylpalmitate g) Butylated hydroxytoluene (BHT);h) Docosapentaenoic Acid (BHA) and i) Tertiary Butyl hydroquinone(TBHQ). The hydrophilic antioxidant or sequesterant includes hydrophilicphenolic antioxidants including at least one of grape seed extract, teaextracts, ascorbic acid, citric acid, tartaric acid, and malic acid inanother aspect.

A method of manufacturing a Salvia hispanica L. derived seed oil inanother non-limiting example is set forth. The seed oil comprises from60-88% PUFAs in a ratio of from 3.1:1-3.3:1 of alpha-linolenic acid(ALA) to linoleic acid (LA), 4-10% of C-18 mono-unsaturated fatty acid,1-5% of C-18 saturated fatty acid and 4-8% of C-16 saturated fatty acidin a mixed triglyceride form that is stable at room temperature for12-24 months and includes antioxidants. The method includes milling orroller press flaking Salvia hispanica L. seed in the absence of oxygento obtain a desired particle size distribution with or without theaddition of hydrophilic or lipophilic antioxidants during the particlesizing process. The resulting biomass is subjected to supercriticalfluid CO² extraction in the presence of lipophilic and/or hydrophilicantioxidants. Any resulting seed oil fractions are collected. The wateris separated in each fraction.

Any resulting seed oil fractions can be treated with additionalantioxidants to afford a desired room temperature stability. The extentof oil extraction can be controlled by particle size distribution of themilled or flaked seed. Propane can be added in mixture withsupercritical CO² in the supercritical state as an extraction solvent.In yet another aspect solvent can be extracted using hexane extractionat or near atmospheric pressures and the resulting boiling point ofhexane in the absence of oxygen, separating the resulting water from theoil/hexane mixture and removing the hexane solvent by distillation at orbelow atmospheric pressure in the absence of oxygen.

Lipophilic antioxidants can be added to increase the room temperaturestability of the resulting oil. The lipophilic antioxidants can be addedeither alone or in combination with at least one of a) phenolicantioxidants including at least one of sage, oregano, and rosemary; b)tocopherol, c) tocotrienol(s), d) carotenoids including at least one ofastaxanthin, lutein, and zeaxanthin; e) ascorbylacetate; f)ascorbylpalmitate g) Butylated hydroxytoluene (BHT); h) DocosapentaenoicAcid (BHA) and i) Tertiary Butyl hydroquinone (TBHQ). The resultingdewatered seed oil can be treated with bleaching clay or activatedcarbon.

Pre-milled or roller press flaked seed can be treated with a lipophilicor hydrophilic antioxidant(s) prior to solvent extraction. Thehydrophilic antioxidant or sequesterant can be formed from hydrophilicphenolic antioxidants including at least one of grape seed extract, teaextracts, ascorbic acid, citric acid, tartaric acid, and malic acid.

A method of mitigating or preventing cardiovascular disease, arthriticpain and inflammation, platelet aggregation, or treating dry eyesyndrome, premenstrual symptoms or modifying immune response in humansor animals is set forth by applying an effective amount of the dietarysupplement, food or beverage to which has been a composition mixedtherewith and comprising a Salvia hispanica L. derived seed oilcomprising from 60-88% PUFAs in a ratio of from 3.1:1-3.3:1 ofalpha-linolenic acid (ALA) to linoleic acid (LA), 4-10% of C-18mono-unsaturated fatty acid, 1-5% of C-18 saturated fatty acid and 4-8%of C-16 saturated fatty acid in a mixed triglyceride form that is stableat room temperature for 12-24 months and includes antioxidants.

In one aspect, an emulsifying agent is added. In another aspect, nano-and/or micro-particles of rice or sugarcane based polycosanol aredispersed for enhancing a heart healthy dietary supplement. A stabilizedoil in a fruit juice concentrate, fruit puree or other water basedflavoring is dispersed in the presence of maltodextrin, or othercarbohydrates, and a suitable emulsifying or emulsion stabilizationagent that is vacuum spray dried to form an amorphous or crystallinesolid suitable for use as a flavoring ingredient carrying stabilizedPUFAs in flavored dietary supplements, foods and beverages. In yetanother aspect, oil based flavors and fragrances suitable for use as aningredient in foods, beverages and cosmetics are added. ALA and LA arealso added as essential fatty acids.

In accordance with a non-limiting example, it has also been found thatthe use of a perilla seed oil extract instead of the disclosed chia seedoil extract is advantageous and contains a very favorable ratio of ALAto LA (omega-3 to omega-6) of as high as about 6:1 in some examples ascompared to chia seed oil that is typically about 3.3:1 ALA to LA.Perilla seed oil extract as obtained, in accordance with a no-limitingexample, is thus an even healthier source of omega-3 than chia seed oilin various non-limiting examples. The manufacturing techniques asdescribed above may equally be applied to the perilla seed oil extractproduction.

FIG. 1 is a flowchart showing a production diagram for a sequence ofsteps for producing omega-3 chia seed oil such as sold under thetradename Chia Gold™ by Valensa International of Eustis, Fla. The salviahispanica seed is provided (block 100) and seed cracking occurs (block102) to form a cracked biomass. Various techniques for seed cracking andforming the biomass can be used as described above. The supercriticalCO² extraction (block 104) uses ultra high pressure carbon dioxideextraction technology and supplied CO² (block 106) such as the DEEPEXTRACT® manufacturing process developed by Valensa International ofEustis, Fla. The defatted seed as a flour, for example, (block 108) isproduced. Separation of the different portions occurs such as byfractionating the seed oil extract (block 110) as described above. Theextract is collected (block 112). Dewatering and decantation occurs(block 114) and antioxidants are added (block 116) such as the OTB® PerOxidation blocker system from Valensa International. Quality controlanalysis occurs (block 118) and the final oil packaged (block 120).

FIG. 2 shows a second production diagram as a flowchart for producingthe perilla seed oil extract in accordance with a non-limiting example.The process begins with a source of the perilla seed also known asperilla frutescens seed (block 130). Similar to the process with theomega-3 chia seed oil, seed cracking occurs (block 132) to form acracked seed biomass followed by the extraction (block 134) using thesupercritical CO² extraction and supplying carbon dioxide (block 136) toproduce the defatted seed (block 138) that is partially or whollydefatted perilla seed as a cake residue with virtually no fat or oil.The other portion is the oil and the CO² is reclaimed (block 140).Similar to the omega-3 chia seed oil, the extract is collected (block142) and dewatering and decantation occurs (block 144). Antioxidantssuch as the OTB® components as described before are added (block 146)and the quality control analysis occurs (block 148) followed bypackaging (block 150).

The perilla seed extract can have a range of values for its fatty acidprofile. Total fatty acids, peroxide values and other component valuesare described in Table 1 below showing an analysis of perilla seedextract and various parameters, specifications and results as anon-limiting example. Results can vary of course for different samples.

TABLE 1 Ingredients: Perilla (Perilla frutescens (L) Britton) Seed Oil,O2B ™ Botanical peroxidation blocker including refined nonGMO soybeanmixed tocopherols and spice extract. Parameter Specification ResultDescription Clear yellow oil, pourable Conforms at room temperature OdorMild Conforms Solubility Insoluble in water, miscible Conforms with oilsFatty Acid Profile [%] VQP-050 (GC) Palmitic Acid 6.3 Stearic Acid 1.9Oleic Acid 22.3 Linoleic Acid 9.7 α-Linolenic Acid >56 59.8 Total FattyAcids (% w/w) 85 . . . 95 88.6 Peroxide Value (meqO₂/kg) <10 VQP-049 2.3Water Content (%)  <1.5 VQP-048 <0.2 Heavy Metals (ppm) <10 ICP-MS <1Microbiological Data (cfu/g) Total Aerobic Microbial Count <10³ USP <61><100 Combined Yeast & Mold <10² USP <61> <100 E. coli/Total Coliforms<10 AOAC 991.14 <10 (all values as is basis) All of the ingredients areGMO free. Therefore this product is in accordance with EU regulations1830/2003 and 1820/2003. The Product has not been treated with gammarays.

Table 2 show accelerated stability testing of the perilla seed extractwith an OTB® per oxidation blocker and Table 3 shows the acceleratedstability testing of a perilla seed extract sample produced by ValensaInternational of Eustis, Fla. as compared to chia seed extracts such asthe Chia Gold™ which is produced by the process shown in FIG. 1 and theTresalbio Chia Oil.

TABLE 2 Accelerated Stability Testing of Valensa Perilla Seed Extractwith O2B^(⊖) Rancidity Induction Time Shelf Life @20° C. (hr)¹ (yr)²Perilla Oil (without O2B) 7 0.5 Perilla Oil (with O2B) 42 2.8 ¹Rancimatinduction time measured in hours with air bubbling through heated oil(90° C.) in the light. ²Rancimat data is a function of accelerated highheat and oxygen exposure. Extrapolated data plots are assumed linear inthe presence of air and light at 20° C. however, if product is stored at20° C. in an air and light barrier package, then shelf stability is atleast doubled.

TABLE 3 Accelerated Stability Testing of Valensa Perilla Seed and ChiaSeed Extracts with O2B^(⊖) Shelf Rancidity Shelf Life Induction TimeLife @20° C. Increase (hr)¹ (yr)² (%) Perilla Oil (without O2B) 7 0.5Perilla Oil (with O2B) 42 2.8 611% Tresalbio Chia Oil (without 12 0.4O2B) Tresalbio Chia Oil (with O2B) 73 2.2 603% ChiaGold Oil (withoutO2B) 9 0.3 ChiaGold Oil (with O2B) 60 1.8 663% ¹Rancimat induction timemeasured in hours with air bubbling through heated oil (80-90° C.) inthe light. ²Rancimat data is a function of accelerated high heat andoxygen exposure. Extrapolated data plots are assumed linear in thepresence of air and light at 20° C. however, if product is stored at 20°C. in an air and light barrier package, then shelf stability is at leastdoubled.

Table 1 illustrates various values and shows the total fatty acids (%w/w) is about 85 to about 95 and has in that particular example a resultof 88.6. It should be understood that the seed oil could possibly haveas low as about 60% w/w of PUFAs and as high as about 95% and a ratio offrom about 4:1 to about 6:1 ALA to LA. The peroxide value of the seedoil is typically under 10.0 meq/Km. The PUFAs typically comprise atleast greater than 50% ALA and in the example shown in Table 1 isgreater than 56% and in one particular example shown in FIG. 1 is 59.8.The seed oil is shelf stable at room temperature up to 32 months in aparticular example. Other data is shown such as specific components ofthe fatty acids and the water content, heavy metals in PPM, andmicrobiological data in CFU/G, such as the total aerobic microbialcount, a combined yeast and mold and E. coli/total coliforms. All thevalues are an as-is basis and the ingredients are GMO free. Therefore,this product is in accordance with EU regulations 1830/2003 and1829/2003. This product had not been treated with gamma rays.Ingredients include the perilla (perilla frutescens (L) Britton) seedoil, OTB® botanical per oxidation blocker including refined non-GMOsoybean mixed tocopherols and spice extracts. GMO corresponds togenetically modified organisms, and thus, non-GMO refers tonon-genetically modified organisms. The soybean had not been createdthrough gene-splicing techniques of biotechnology or geneticengineering.

The production diagram in FIG. 2 shows the process used to obtain theperilla seed extract in accordance with a non-limiting example. Theextraction technology as described relative to the chia seed oil andextract in the incorporated by reference application and described abovein some detail may be used. It should be understood that extractiontechnology creates materials for human nutrition and supplementation andoffers various benefits including enhanced efficacy with the isolationof key components to allow higher dosage and targeted performance.Extraction allows standardization. Natural materials tend to vary inmake-up and extraction makes them consistent. It is also convenientbecause smaller dosages of high efficiency materials allow a consumer tomore easily obtain the required levels of nutrients in a daily regimen.There is also enhanced safety because extraction gives more of thedesired products and less of what is not desired. Extraction allows theremoval of compounds that are not optimal for human health from naturalmaterials.

The desired extraction technology uses the DEEP EXTRACT® process fromValensa International as an ultra high pressure carbon dioxideextraction technology that yields micronutrients and has high extractionefficiency to deliver more of the higher molecular weight compounds thatmore closely track the natural source materials. The process is flexibleand allows for possible fractionation of the product if desired anddelivery of specific compounds out of the raw material.

This extraction process, such as the DEEP EXTRACT® process, offers amore gentle treatment of high value raw materials at temperature levelsthat are substantially below those used in other expeller pressprocesses and some chemical solvent extraction processes in the absenceof oxygen. This reduces the degradation of liable compounds, chemicalchange of a component and the oxidation potential. The supercritical CO²process offers virtual sterilization of the finished product andbiomass, which are untouched by chemical solvents and stay “natural” asbefore extraction. Selective fractionation in some example isadvantageous. Pressure is a main tool used to tailor the resultingfractionated products for product quality and efficient manufacturing.Because the CO² extraction is an all-natural and organic process, thefinal product is devoid of impurities and residues and delivers throughthe supercritical CO² extraction the high molecular weight compoundssuch as sterols, carotenoids and long chain alcohols.

Supercritical CO² extraction is advantageous over other methods used forextracting botanicals, including tinctures (usually alcohol extraction;steam distillation; expeller pressing, sometimes referred to as “coldpressing,” and chemical solvent extraction). Chemical solvent extractiontechnology using strong solvents and supercritical CO² technology usinghigh pressures typically offer the most comprehension extraction of abotanical. Supercritical CO² extraction conducted under very highpressure is advantageous. When carbon dioxide gas (CO²) is compressedabove 73 bar at a temperature above 31 degrees C. (87.8 degreesFahrenheit), it transforms into a dense gas as supercritical CO², whichhas an extremely high solvating capacity and a power to extractconstituents of botanicals. Its solvating capacity is a function of itsdensity and by changing its density with pressure, the manufacturer isable to select the quality, quantity and specific principles of thetargeted extract. Supercritical CO² is biologically compatible andgenerally regarded as safe (GRAS) by the FDA. It is also non-flammableand environmentally sound. Any defatted cake resulting from thesupercritical CO² process may be viable and can be marketed or used forfurther processing in a wide range of human/food applications. As willbe explained below, the perilla cake that is partially defatted isprocessed during supercritical extraction to form a flour that can beused as a dietary supplement, food or beverage.

The supercritical CO² process offers a gentle treatment of high valueraw materials at temperature levels substantially below those used inexpeller press in some chemical solvent extraction operations in theabsence of oxygen. This reduces the degradation of labile compounds,chemical changing components and the oxidation potential. Thesupercritical CO² process offers virtual sterilization of the finishedproduct and biomass that are untouched by chemical solvents and stay“natural” as they were before extraction. It also allows the advantageof fractionating the extracted components selectively with pressuretailoring the resulting fractionated products for product quality andefficient manufacturing. This addresses pesticide/insecticide residuesand handle concerns about microorganisms that are present in expellerpress materials.

The perilla extract as shown in the flowchart of FIG. 2 is dewatered anddecantated and antioxidants added such as the Valensa OTB® per oxidationblocker system as a stabilizer to ensure that the botanical extractreaches a consumer in an efficacious and safe form. Stabilization withthe OTB® components is a key to shelf life and continued product qualityand is advantageous over using preservatives to stabilize naturalmaterials, which is often seen as a negative by consumers. The OTB® peroxidation blocker system used by Valensa is 100% natural, non-GMO, andprotects sensitive oils and particularly the highly unsaturated oilsderived from fish and botanicals from the manufacture to consumption. Itmay also be used to protect the perilla flour as the leftover residuefrom supercritical CO² extraction. The OTB® per oxidation blacker is asynergistic proprietary formulation of powerful natural compoundsincluding astaxanthin, phenolic antioxidants and natural tocopherols.This technology prevents destructive oxidative, photochemical andrancification reactions. It protects expensive and sensitive compoundssuch as carotenoids and polyunsaturated fatty acids and can boost theeffectiveness of other antioxidants such as vitamin E because itchemically quenches stable vitamin E free radicals. The antioxidantshave in-vivo activity to protect both products and people.

Perilla has a number of essential oils. These are extracted from theleaves of perilla. About 50% to about 60% of perillaldehyde isresponsible for so much of the aroma and taste of perilla. There areother terpenes such as limonene, caryophyllene and farnesene. There areother chemotypes such as perilla keytone (PK), esholzia keytone (EK),perillene (PL), and various phenylpropanoids such as myristicin,dillapiole and elemicin. Citral is a type rich in rosefuran. Perilla oiltypically is obtained by pressing the seeds of perilla that containabout 35% to about 45% oil. In some parts of Asia, perilla oil is anedible oil valued for medicinal benefit. Typically, perilla oil is arich source of omega-3 fatty acid alpha-linolenic acids. As a dryingoil, it is similar to tung oil or linseed oil and is sometimes used inpaint, varnish, linoleum, printing ink, lacquers and other protectivewaterproof coatings. In Japan, the oxime of perillaldehyde (perillartin)is used as an artificial sweetener and typically is about 2,000 timessweeter than sucrose.

Rancimat testing has shown the advantages of the perilla seed oilextract in accordance with a non-limiting example. This method is anaccelerated oxidation test that is a simple, quick and efficient way toscreen the effectiveness of the antioxidants used in liquid fats andoils. Typically, the rancimat test is an accelerated oxidation test inwhich the oil or fat to be tested is run at an elevated temperatureexposing the sample to air accelerating the oxidation process of theoil. Auto oxidation typically occurs in a few hours instead of themonths or years and the metabolites are driven off into a measuringvessel that measures the change in conductivity in one example. Thiswould indicate the point at which the formation of volatile carboxylicacids and oxidation has occurred.

It is also possible to disperse nano- and/or micro-particles of rice orsugar cane based policosanol for providing a heart healthy dietarysupplement. Such dietary supplement composition additives are disclosedin commonly assigned U.S. Pat. No. 7,959,950, the disclosure which ishereby incorporated by reference in its entirety. This human or animaldietary supplement composition includes one or more long chain (C24-C36)primary alcohols (policosanols) dispersed in food-grade oils or fatswhere the average policosanol particle size is greater than 2 micronsand less than 10 microns in one example, and in another example, lessthan 100 microns.

There now follows further details of the composition of matter inaccordance with a non-limiting example that is formed as a shelf stable,partially defatted supercritical CO2 fluid solvent extracted whole grainflour derived from the cracked biomass of perilla frutescens. In oneexample, the flour is formed of minerals and includes about 2 to 8percent of native seed oil and about 35 to 45 percent protein and about35 to 45 percent fiber. In one example, the native seed oil is formed ofabout 1 to about 4 percent ALA and about 0.2 to 0.8 percent LA and inanother example, the fiber is about 32 to about 40 percent insolublefiber and from about 2 to about 6 percent soluble fiber. In anotherexample, the composition exhibits pH dependent thixotropic propertieswhen mixed with water. In another example, the flour is formed oflipophilic additives, such as at least one of rosemary oil, tocopherols,tocotrienols, carotenoids, seed oils, lipophilic solvent extractedbotanical oils, lipophilic food flavorings, polyunsaturated fatty acidesters. Hydrophilic additives can include hydrophilic solvent extractsof botanicals, green tea extract, grape seed extract, ascorbic acid,caffeine, mono and/or polysaccharides, gums, phospholipids, biopolymers,or hydrophilic food flavorings.

In another example, about 2 to about 3 percent fructo-oligosaccharidescan be used such as forming an antioxidant. The OTB® per oxidationblacker system may be used as described above. A delivery product can beused with the composition that is formed as a beverage, protein shake,nutritional bar, confectionary filling, icing, pasta, processed meat,peanut butter or jelly. This composition may be added to a dietarysupplement, food or beverage and used to treat gastrointestinalirregularities or cardiovascular disease in humans or animals. It can beformed as a beverage, liquid concentrate or dried beverage premixed towhich the composition is added. In another example, a liquid concentrateor dried premix can be formed that includes protein shakes, fruitsmoothies, ready-to-drink beverages, dried beverage pre-mixes, frozenfruit concentrates, aqueous alcoholic beverage premixes, concentrates ortheir dried pre-mixes, vitamin, carbohydrate and protein fortified mealreplacement beverages, drinkable dairy and non-dairy yogurts, graviesand dried gravy pre-mixes and ready-to-drink and dried pre-mixed infantformulas. The final beverage may be thickened by adding one or moreacidulants for adjusting the pH from between about 3 to about 6.5.

FIG. 3 shows a production diagram as a flowchart for producing thedescribed composition of matter as a shelf stable, partially defattedsupercritical CO2 fluid solvent extracted whole grain flour that isderived from the cracked biomass of perilla frutenscens. As illustrated,the process starts (block 158) and the perilla frutenscens seed isobtained (block 160) for further processing. The seed is cracked (block162) and subject to extraction (block 164) using the supercritical CO2fluid solvent extraction followed by CO2 separation (block 166) andcarbon dioxide recycling (block 168). The seed oil is obtained (block170). The defatted grain is collected (block 172) and packaged (block174) and then subject to quality control analysis (block 176). Theprocess ends (block 178).

The product specification for the composition in one non-limitingexample follows:

Ingredient: Perilla (Perilla frutescens) seed (partially defatted withsupercritical CO₂) Kosher certified by KSA; IFANCA Halal PhysicalAppearance Brown-beige coarse powder Taste Mild Bulk Density 0.15-0.25g/mL Chemical Fat 2-8% Hexane Soxhlet Omega-3 (ALA) 1-4 g/100 g (as-is)GC-FAME Protein 35-45% Fiber 35-45% Pesticides No detectable pesticideresidues CDFA or similar (>RL) on seed raw material used to manufactureproduct Microbiological USP <61> Total Plate Count max. 10⁴/g Yeast/Moldmax. 10³/g E. coli/Coliforms <10/g

Although hexane soxhlet is disclosed, it should be understood thatdifferent extraction may be used. It should be understood that a rangeof values is given. These values may vary even more by as much as twentypercent.

There now follows a representative analysis of the composition as anomega-3 low fat whole grain flour.

Ingredient: Perilla (Perilla frutescens) Seed (partially defatted withsupercritical CO₂) Dietary Calories 220 kcal/100 g Fat   4 g/100 gSaturated Fat 0.3 g/100 g Monounsaturated Fat 0.8 g/100 g Omega-3 ALA  2 g/100 g Omega-6 LA 0.4 g/100 g Total dietary fiber RDI (25 g)  40g/100 g Insoluble fiber  36 g/100 g Soluble fiber   4 g/100 g Minerals:US RDI (mg) mg/100 g Sodium 2400 3 Potassium 3500 1100 Calcium 1000 680Iron 18 <1 Phosphorus 1000 3 Magnesium 400 500 Arsenic — <0.5 Mercury —<0.5 Cadmium — <0.5 Lead — <0.5 Ash 6.4% Amino acids: g/100 g alanine1.7 arginine 4.4 aspartic acid 3.1 cysteine 0.6 glutamic acid 6.8glycine 1.8 histidine 1.0 isoleucine 1.4 leucine 2.4 lysine 1.4methionine 0.7 phenylalanine 1.9 proline 1.3 serine 1.9 threonine 1.3tryptophan 0.6 tyrosine 1.4 valine 1.8 Protein (Kjeldahl)  42 g/100 g

The ingredient listing with dietary calories, fat, total dietary fiber,minerals, including ash and amino acids, have specific numbers as anon-limiting example, but these numbers can vary by as much as 10 toabout 25 percent depending upon the final product and processingparameters used during the supercritical fluid extraction processing.The parameters of the superfluid processing can be varied to form thefinal product depending on what final product composition is desired.Pressure is one particular parameter that can be varied to form aselected final product. Also, the nature of the milling or roller pressflaking of the perilla frutenscens seed to obtain a cracked seed biomasscan be varied to form the final product. The amount of cracking can berelevant to the amount of extraction during the supercritical fluidextraction process. Also, fractionation may be used during the CO²extraction as described above. The CO² extraction such as used by theassignee Valensa has a high solvating capacity that is a function ofdensity. By changing the density (with pressure), the CO² extractor isable to select the quality, quantity and specific principles of thetargeted extract and flour. The output from the supercritical CO²extractor depends on the change in density, pressure and other extractorparameters. For example, it is possible to fractionate during thesupercritical CO² extraction in separate pressure step-down stages andlight and heavy fractions of seed oil extract collected, but with theflour being separate.

In accordance with non-limiting aspects, it has been found that thepartially defatted perilla derived whole grain flour is stable. Thisresulting flour's stability serves as a stable delivery platform for theessential fatty acid esters of ALA, LA, protein, soluble and insolublefiber, minerals such as calcium, potassium, magnesium and phosphorus,and both lipophilic and hydrophilic additives, which is free ofcyanogenic glycosides, vitamin B antagonists, lignin and gluten. Theresulting flour can be used as a food ingredient in a beverage and as adietary supplement ingredient to various foods. This perilla derivedflour can provide beneficial results in enhancing gastrointestinalregularity and heart health.

The resulting partially defatted whole grain perilla derived flour mayexhibit an ability to reabsorb large quantities of lipophilic as well ashydrophilic additives while exhibiting a pH dependent thixotropic effectin aqueous environments. The flour may be formed as a food or beverageor dietary supplement ingredient and operate as a delivery vehicle forlipophilic and hydrophilic additives in the presence of protein, fiber,various levels of the essential fatty acid esters of ALA and LA andminerals that are free of cyanogenic glycosides, vitamin B antagonists,lignin and gluten.

In accordance with a non-limiting aspect, the resulting perilla derivedflour may enhance the protein, fiber, mineral content and pH controlledviscosity of beverages and their liquid concentrates, dried beveragepre-mixes including protein shakes and fruit smoothies, ready-to-drinkbeverages, beverage pre-mixes, frozen fruit concentrates, alcoholicbeverage dry pre-mixes and concentrates, meal replacement beverages,drinkable dairy and non-dairy yogurts, gravies and dry gravy pre-mixes,and ready to drink and dried pre-mixed infant formulas.

The resulting seed meal as a flour provides a unique blend of protein,insoluble and soluble fiber, and variable amounts of the essential fattyacid triglycerides of alpha-linolenic acid (omega-3, “ALA”) and linoleicacid (omega-6, “LA”).

The resulting flour can be incorporated into beverages, dry beveragepre-mixes, liquid or frozen beverage concentrates and the like with theadded feature of pH controlled viscosity by either the amount of perilladerived meal or flour that is added and/or by optionally lowering the pHwith an acidulant to improve further the viscosity of the resultingbeverage.

In one aspect, the perilla derived flour is added to a beverage, liquidconcentrate, or dried beverage pre-mixes. The flour may be used forprepared beverages, their liquid concentrates, and dried pre-mixes,including protein shakes, fruit smoothies, ready to drink beverages, drybeverage pre-mixes, frozen fruit concentrates, aqueous alcoholicbeverage pre-mixes, concentrates or their dried pre-mixes, vitamin,carbohydrate and protein fortified meal replacement beverages, drinkabledairy and non-dairy yogurts, gravies and dry gravy pre-mixes, and readyto drink and dried pre-mixed infant formulas. The flour may includeadded lipophilic additives and added hydrophilic additives. The pH rangemay be adjusted with the addition of one or more acidulants to bring thepH of the final product to a pH of from about 3 to about 6.5 in anexample to further thicken the resulting beverage in one non-limitingexample.

The flour may be added to a beverage and prepared in a pasteurizedbeverage form. In its use, it is shelf stable and contains sterilizedwhole seed in an admixture with a wide range of liquid beveragecomponents, including but not limited to, for example, fruit derivedjuices, water or natural or artificially flavored water such as colas,coffees, teas and the like. It can contain a sweetener such as sucrose,fructose corn syrup or an artificial sweetener. It can also containpreservatives such as sodium benzoate and such other additives common tobeverage formulations. The resulting beverage may exhibit a pH dependentviscosity. The resulting beverage may be rich in fiber and isparticularly useful for maintaining good gastrointestinal systemregularity in a convenient and tasty beverage form while deliveringheart healthy polyunsaturated fatty acids, protein and minerals.

The beverage can be enriched in protein, polyunsaturated essential fattyacid triglycerides, minerals and rich in fiber particularly useful formaintaining good gastro-intestinal system regularity in a convenient andtasty beverage form while delivering heart healthy polyunsaturated fattyacids, protein and minerals requiring no additional thickening agents.It can be useful for the control of hunger via satiety requiring noadditional thickening agents to effect such satiety.

The resulting flour can be incorporated into beverages, dietarysupplement bars, nutritional bars, baked goods, confectionary fillings,icings, processed meats, peanut butter, jellies and the like as deliveryvehicle for quantities of the essential fatty acid esters of ALA and LA,protein, soluble and insoluble fiber, and minerals depending on theamount of ALA and LA retained in the partially defatted flour and theamount of the flour employed in the end user formulation.

In addition, the resulting partially defatted whole grain flour iscapable of re-absorbing and stabilizing relatively large quantities ofother lipophilic compounds providing a convenient vehicle for deliveryof these compounds in addition to ALA, LA, protein, insoluble fiber andminerals as an ingredient in food, beverage and dietary supplement basedformulations. In one example, the partially defatted whole grain flourcan reabsorb lipophilic compounds of from about 1 to about 25 percent ofthe weight of the partially defatted whole grain flour, depending on thelevel of native seed oil remaining in the solvent extracted, whole grainflour.

In an example, the resulting flour also exhibits unique pH dependentthixotropic properties when added to aqueous based formulations such asbeverages, including protein-based smoothies. It also provides a uniquemethod or process for mitigating the undesirable free water associatedwith nutritional and dietary bar production, while providing ALA, LA,protein, soluble and insoluble fiber and minerals to such formulationsand providing other lipophilic compounds depending on the composition ofthe flour employed.

In one aspect, the flour is used with a beverage or protein shake“smoothie” or nutritional bar or dietary supplement bar enriched inprotein, fiber, minerals and a controlled portion of ALA and LA. Theflour also can be used with a confectionary filling enriched in protein,fiber, minerals and a controlled portion of ALA and LA. It can also beused with an icing or processed meat or peanut butter or jelly enrichedin protein, fiber, minerals and a controlled portion of ALA and LA.

The flour can also be used with a chocolate, pectin or gelatin basedconfectionary or dietary supplement whose inner filling, outer shell orintegrated composition is enriched in protein, fiber, minerals and acontrolled portion of ALA and LA. It can be used with a pasta enrichedin protein, fiber, minerals and a controlled portion of ALA and LA.

As noted before, using the super-critical CO₂ fluid extraction method ofpreparation, the resulting flour can be incorporated into beverages,dietary supplement bars, nutritional bars, baked goods, confectionaryfillings, icings, processed meats, peanut butter, jellies and the likeas a partially soluble delivery vehicle for heart healthy quantities ofthe essential fatty acids ALA and LA, protein and soluble and insolublefiber depending on the amount employed in the end user formulation.

In another aspect, the flour can include lipophilic compounds reabsorbedinto the flour including one of at least rosemary oil, tocopherols,tocotrienols, carotenoids, seed oils, lipophilic solvent extractedbotanical oils, lipophilic food flavorings or other health or functionalhydrophilic compounds.

In another aspect, the flour can include hydrophilic additivesre-absorbed into the flour such as, for example, hydrophilic solventextracts of botanicals, green tea extract, grape seed extract, ascorbicacid, caffeine, mono and/or polysaccharides, gums, phospholipids,biopolymers, hydrophilic food flavorings or other health or functionalhydrophilic compounds. In yet another aspect, the flour may include asuitable proteolytic enzyme or plurality of enzymes to produce a novelprobiotic mixture rich in essential amino acids. It can also be treatedwith a suitable cellulase or amylase enzyme or enzymes, which degradesthe soluble and insoluble fiber to produce a novel probiotic mixturerich in digestible monosaccharide and oligosaccharide units in anotherexample.

The resulting perilla derived flour can also be incorporated intobeverages, dietary supplement bars, nutritional bars, baked goods,confectionary fillings, icings, processed meats, peanut butter, jellies,bakery goods and the like as a delivery vehicle for protein, soluble andinsoluble fiber and minerals or as a desiccant in food applicationswhere excess water creates a formulation problem.

Many modifications and other embodiments of the invention will come tothe mind of one skilled in the art having the benefit of the teachingspresented in the foregoing descriptions and the associated drawings.Therefore, it is to be understood that the invention is not to belimited to the specific embodiments disclosed, and that themodifications and embodiments are intended to be included within thescope of the dependent claims.

That which is claimed is:
 1. A composition for treating gastrointestinalirregularities or cardiovascular disease comprising an effective amountof a shelf stable, partially defatted supercritical CO2 fluid solventextracted residue remaining after oil extraction derived from a crackedbiomass of perilla frutescens, the perilla derived residue comprisingminerals and 2 to 8 percent of native seed oil, 35 to 45 percentprotein, and 35 to 45 percent fiber, and an effective amount of addedlipophilic and/or hydrophilic antioxidant stabilizers including phenolicantioxidants as a preservative that extend the shelf life of thecomposition, wherein the perilla derived residue is made by crackingperilla frutescens seed into a cracked seed biomass, subjecting thecracked seed biomass to supercritical CO2 extraction in the presence ofthe lipophilic and/or hydrophilic antioxidant stabilizers including thephenolic antioxidants and within a supercritical fluid extraction unitto produce a seed oil extract, removing the seed oil extract from thesupercritical fluid extractor unit, and collecting the left over residueremaining in the supercritical fluid extractor unit after oil extractionto form the residue.
 2. The composition according to claim 1, whereinthe native seed oil comprises 1 to 4 percent Alpha-Linolenic Acid (ALA)and 0.2 to 0.8 percent Linoleic Acid (LA).
 3. The composition accordingto claim 1, wherein the fiber comprises 32 to 40 percent insoluble fiberand 2 to 6 percent soluble fiber.
 4. The composition according to claim1, further comprising lipophilic additives comprising at least one ofrosemary oil, tocopherols, tocotrienols, carotenoids, seed oils,lipophilic solvent extracted botanical oils, lipophilic food flavorings,polyunsaturated fatty acid esters.
 5. The composition according to claim1, further comprising hydrophilic additives comprising at least one ofhydrophilic solvent extracts of botanicals, green tea extract, grapeseed extract, ascorbic acid, caffeine, mono and/or polysaccharides,gums, phospholipids, biopolymers, or hydrophilic food flavorings.
 6. Thecomposition according to claim 1, further comprising 2 to 3 percent offructo-oligosaccharides.
 7. The composition according to claim 1,further comprising a delivery product comprising a beverage, proteinshake, nutritional bar, confectionary filling, icing, pasta, processedmeat, peanut butter or jelly.
 8. A composition for treatinggastrointestinal irregularities or cardiovascular disease comprising aneffective amount of a shelf stable, partially defatted, supercriticalCO2 fluid solvent extracted residue remaining after oil extractionderived from a cracked biomass of perilla frutescens, the perilladerived residue comprising minerals and 2 to 8 percent of native seedoil, 35 to 45 percent protein, and 35 to 45 percent fiber, and aneffective amount of lipophilic and hydrophilic antioxidant stabilizersincluding phenolic antioxidants as a preservative that extend the shelflife of the composition wherein the perilla derived residue is made bycracking perilla frutescens seed into a cracked seed biomass, subjectingthe cracked seed biomass to supercritical CO2 extraction in the presenceof the lipophilic and/or hydrophilic antioxidant stabilizers includingthe phenolic antioxidants and within a supercritical fluid extractionunit to produce a seed oil extract, removing the seed oil extract fromthe supercritical fluid extractor unit, and collecting the left overresidue remaining in the supercritical fluid extractor unit after oilextraction to form the residue.
 9. The composition according to claim 8,wherein the native seed oil comprises 1 to 4 percent Alpha-LinolenicAcid (ALA) and 0.2 to 0.8 percent Linoleic Acid (LA).
 10. Thecomposition according to claim 8, wherein the fiber comprises 32 to 40percent insoluble fiber and 2 to 6 percent soluble fiber.
 11. Thecomposition according to claim 8, further comprising lipophilicadditives comprising at least one of rosemary oil, tocopherols,tocotrienols, carotenoids, seed oils, lipophilic solvent extractedbotanical oils, lipophilic food flavorings, polyunsaturated fatty acidesters.
 12. The composition according to claim 8, further comprisinghydrophilic additives comprising at least one of hydrophilic solventextracts of botanicals, green tea extract, grape seed extract, ascorbicacid, caffeine, mono and/or polysaccharides, gums, phospholipids,biopolymers, or hydrophilic food flavorings.
 13. The compositionaccording to claim 8, further comprising 2 to 3 percent offructo-oligosaccharides.
 14. The composition according to claim 8,further comprising a delivery product comprising a beverage, proteinshake, nutritional bar, confectionary filling, icing, pasta, processedmeat, peanut butter or jelly.